The Bennington Chamber of Commerce, officially known as the Southwestern Vermont Chamber of Commerce, plays a vital role in promoting and enhancing the business environment in the Southwestern Vermont region, including the Shires. Their mission is focused on advocating and leading a unified effort to maintain and improve a healthy business climate and a rewarding quality of life in the area. They aim to grow businesses, foster stable growth in the region's creative ecosystem, build safe and healthy communities, and market Southwestern Vermont to a diverse audience​.

Joining the Chamber offers numerous benefits, making it an attractive option for businesses and non-profits. Some top reasons to become a member include access to networking opportunities through events, seminars, and gatherings that facilitate connections and potential partnerships. Members gain increased business exposure via the Chamber's directory and promotional materials. The Chamber also provides advocacy and support, representing business interests at various governmental levels and offering resources for navigating regulatory challenges. Educational resources in the form of workshops and training sessions are available to help businesses develop and grow. Additionally, membership enables community involvement, offering exclusive benefits and discounts, and contributes to marketing the region. The Chamber also empowers young professionals and fosters credibility and trust for businesses through its reputable presence​.

Some notable local chamber events include the "Heart of The Shires Luncheon 2023," "Women In Leadership Luncheon 2023," and "Garlic Town, USA 2023 Preview," which are excellent opportunities for networking, learning, and engaging with the local business community. These events and membership benefits underscore the Chamber's commitment to fostering a dynamic and collaborative business environment in Southwestern Vermont.